Potassium Hydroxide → 2-(2,4-Dichlorophenyl)-3-(1H-imidazol-1-yl)propane-1,2-diol
Reaction equation
ClC1C=CC(C(C(C)C)C([O:11][CH2:12][C:13]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])([OH:20])[CH2:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=O)=CC=1.[OH-].[K+]>CO>[Cl:28][C:22]1[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=1[C:13]([OH:20])([CH2:12][OH:11])[CH2:14][N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (+)-3-[2-(4-chlorophenyl)isovaleroyloxy]-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-2-propanol (2.89 g; M.P., 145°-146.5° C.) in methanol (40 ml) was added a 20% aqueous potassium hydroxide solution (6 ml), and the mixture was stirred at room temperature for 3 hours. The solvent was removed in vacuo, and the oily residue was dissolved in 6N hydrochloric acid (30 ml). The acidic aqueous solution was washed with chloroform (20 ml×2) and then neutralized with a 28% aqueous ammonia solution. The resulting crystals were collected by filtration to give (+)-2-(2,4-dichlorophenyl)-1-(imidazol-1-yl)-2,3-propanediol. Yield, 1.51 g; 81%. M.P., 143° C. [α]D19, -113.1° (C=1.0, MeOH).